Crossdressing
by IchigoHatake
Summary: A short, silly story about May crossdressing as Ash. What happens when he catches her?
1. Chapter 1

Crossdressing

May was invited to Ash's house that day. Ash had led her upstairs to his room, which look like a tornado of old papers and laundry.

Ash's mom called him down and he sighed. He turned to May and said, "Sorry, May. I'll back back in ten minutes. Mom needs me. Just make yourself at home."

Ash then flew out of the room, stirring up a cloud of dust. May coughed and waved her hand, trying to blow away the dust.

"Geez. Would it kill him to clean his room?"

May sat down on his bed, which was the only decently clean part of his room. She sat there for at least five minutes, slowly being bored to death.

She sighed impatiently and glanced over at Ash's closet. It was completely fills with his jackets. May smiled thoughtfully. She'd always wanted to try one on. So why not just throw one on for just a minute?

She peeked out the bedroom door to make sure no one was there, then ran over to his closet, barely managing not to trip on the layers of junk on the floor.

May took one of the jackets off of the hanger and pulled it on over top of her clothes. Then, she walked over to Ash's mirror, which was blanketed in dust.

She grabbed one of the random shirts lying on the floor, and used it to wipe the dust off the mirror. As she saw her reflection in the mirror, she giggled. She looked absolutely adorable in his jacket!

She happily pranced around the room, impersonating Ash, pretending to throw pokeballs and speaking in a boyish voice that sounded almost exactly like Ash.

"May, will you go out with me?" she asked, talking in a boyish voice.

She ran to the other side of the mirror and said, "Of course Ash! I love you!"

Before she could say more, someone tapped her on the shoulder. She slowly turned around and died inside when she saw that Ash was right behind her.

"May, you're in my clothes..." said Ash, completely surprised.

May face flushed red as she nodded in embarassment.

"And you were pretending to be me..."

She nodded again, even more ashamed of herself.

"May, do you like me?" He asked, looking down at the ground.

"Yes..." May admitted, feeling bad, just knowing that he was going to reject her.

"Um...you're impression of me was pretty accurate. I like you too."

May's face lit up as she cheered and spontaneously kissed him.

Once the kiss was over, Ash said, "But if you're going to crossdress like me, then do it when I'm not around."

May smiled and nodded, feeling so happy that he felt the same. Ash smiled at her back, and she could tell that they'd be together forever.


	2. Chapter 2

The crossdressing frenzy wasn't over just yet. Regardless of Ash's wishes, she crossdressed around him all the time. She just felt so weird and happy whenever she wore his jacket.

Her parents knew about her relationship with Ash, but were still weirded out whenever she wore his jacket.

"It's...just weird to us," her mother told her after May had asked why they didn't like her crossdressing.

"Weird how?" May asked, cocking her head to the side.

Her mother just sighed and got back to doing the laundry. May just shrugged it off, and went outside, heading over to Ash's house.

Ash's mom had just gotten him some new Sinnoh style clothes and May wanted to try them on.

She ringed the doorbell once she had arrived and waited patiently. Delia answered after a while and wasn't surprised to see May in Ash's clothing.

"Come on in," said Delia with a warm smile.

May stepped inside and plowed up the staircase, then turn right into Ash's bedroom.

His bedroom had straightened up quite a bit, but there was still hoards of papers and old t-shirts everywhere.

Ash was sitting at his desk and turned around as he heard May walk in. "You heard about my new pair of clothes didn't you?"

May nodded, a childish smile appearing on her face.

"You're such a weirdo. What's with you and crossdressing?"

May just shrugged and ran over to Ash's closet, avoiding the trash scattered across the floor. She threw open the closet door and grabbed the nearest jacket.

She threw off her old jacket and threw on the new one, happily curious about how she would look.

She stood in front of the mirror and posed for a while. She didn't look as good in this as the old one. She looked like a guy with long hair. She stuck out her tongue in disapproval.

"You don't like my clothes?" Ash asked, laughing a little.

"Nope. They only look good on you," she commented, winking at him.

Ash laughed, stood up, and walked over to her, embracing her.

"You are the world's weirdest girlfriend," he said, laughing at how silly she looked in his outfit.

"I might not be your girlfriend for long if you keep being mean to me," she snapped back.

"I was just kidding," Ash said, stroking her beautiful brown hair.

"Ok," said May leaning in closer to Ash.

Their lips locked as she laughed silentlyu in her head. _We always kiss whenever I crossdress _she thought to herself.

That ended the day. May quickly discarded the new jacket and returned to the old jacket. Ash kissed her good-bye and May went home, happy that she had visited him today.

ANOTHER SHORT AND SWEET CHAPTER


	3. Chapter 3

The crossdressing continues. May just can't be stopped. Ash was going shopping for new clothes and she was going to come with him to try on whatever he wanted to buy.

She laughed to herself. She knew she was a weirdo, but she couldn't help it. Being in his clothes just had a certain perk to it.

Ash sulked as May followed him into the store. He still wasn't used to her crossdressing obsession, but he put up with it because he loves her.

Ash grabbed May's hands and lead her over to the clothing section with him. He made a mental not to try and cure her of her obsession later, but not today. She was bent on dressing up today.

May's eye lit up as she saw all the amazing lines of clothing, but the Unova fashion line was what caught her eye.

"You should buy something from the new Unova section," suggested May.

Ash nodded, knowing better than to refuse her wishes and just went along with whatever she wanted.

After searching around for a whole half hour, Ash had had enough and just ripped a random set of clothes of their hanger, and dragged May over to the dressing room with him.

The runner of the fitting rooms, stared judgingly at May as she and Ash both entered a dressing room with the same pair of clothes.

"Pft. Weird kids. Back in my day...," the guy ranted to himself.

Inside May's dressing room, she practically ripped off her clothes, eager to try on the ones they'd just picked out.

She speedily threw on the jacket and shrieked with glee as she stared at her reflection. She winked at herself.

"Hey Sexy!" she giggled to herself.

She had been standing in there for a long time without realizing it, and shrieked when Ash knocked on her door.

"Are you done in there?" he asked impatiently.

"Wanna come in and see?" she teased.

Surprisingly, he did step in there.

"Wha?! What if I was naked and you just walked in like that?!"

"Oh Please," said Ash, rolling his eyes. "You were in here forever. It's obvious that you were just checking yourself out in the mirror."

May huffed in defeat. "Alright. You got me there. Let's check out these clothes."

"Can I check out your lips first?" Ash asked slowly leaning in.

'That'll be one dollar," May teased, leaning forward as well.

Their lips locked locked for a long time, as they passionately kissed.

'She's kind of sexy when she crossdresses' Ash thought to himself.

Ash had finally accepted her. She was his lovable, big eyed, brunette, crossdressing girlfriend, and he LOVED her.


	4. Chapter 4

Comic con was here, and May thought it would be another opportunity to crossdress. As didn't care if she wore his new clothes from Kalos, but still wondered why she was going to crossdress.

"Don't you want to be a super hero or something?" he questioned.

"You ARE my super hero," May countered.

Ash blushed, defeated. He couldn't argue. He WAS kind of a super hero. Some day, he'd be a Pokemon master!

Comic con arrived very soon, and Ash waited impatiently at the entrance for May.

When she came, he blinked in surprise. She didn't look half bad in his clothes.

"Hey Ash! Like my costume?'

"Love it. I feel like I've seen it somewhere before," he said, stroking his chin and pretending to think.

May rolled her eyes, grabbed his hand, and pulled him forward.

"Come on! I wanna buy some pocky!" she said, jumping up and down and whining like a child.

"Okay. Just calm down for two seconds!" he said as he walked in with her, their hands intertwined.

Everyone stared at the happy couple as they walked in, laughing like idiots at some joke that Ash told.

May rushed over to the pocky stand, practically shoving her money in the shop keepers face.

She bought ten boxes. 3 were strawberry and 7 were chocolate. She opened a pack of the chocolate and munched away.

Ash smiled over at her, glad that she was enjoying herself, but his happiness faded as he saw Drew.

"Hey May!" Drew greeted, waving for them to come over.

"Hey Drew! You work at comic con?"

"Yep. Needed some extra money. Hey, I heard that you and Ash are going out."

"Yup. I run wild and he makes sure I don't trip on anything."

"How about you guys enter the love game? It tests the compatibily of partners. We only have two couples signed up and we need a third."

"Let's do it Ash!" exclaimed May, bouncing up and down again.

Ash wasn't all that excited about some dumb love quiz, but agreed to it, knowing that it would please May.

"We'll do it!" May exclaimed, scribbling down their names on the entry list.

'Thanks," said Drew, grabbing the entry form. "Just go through the door to the left and we'll set you up."

The couple was situated on some heart-shaped chairs. They waited patiently as many people gathered to watch the love game.

Drew was the announcer for this, and quickly took his place on the stage.

He positioned the microphone before speaking. "Welcome ladies and gentleman to the love game! We have three lovely couples competing here today. Let's give it up for couple number one, Misty and Tracey!"

A ginger and a kid with brown hair stood up and took a quick bow.

"And here's couple number two...Conway and Dawn!'

"I'm not his girlfriend! He forced me into this!" Dawn cried out.

Conway walked up behind her ans ehispered into her ear, "No one will listen to your screams for help!"

Dawn yelped, running back to her seat and shivering in fear. That Conway guy is a freak.

"And last but not least, Couple number three! Ash and May!"

The crowd cheered as they took a bow. The crowd whistled at May, impressed that she was in her boyfriend's outfit.

"Let the round begin! We'll ask you questions and the guys must answer them correctly. Girls, please be honest if they're right or not. We'll start with Tracey. What is your girls favorite color?"

"Blue?"

'Correct. Next...What are her parents' names?"

"I don't know."

"Wrong. Where is she from?"

"Cerulean."

"Correct. What is her favorite food?"

"Riceballs?"

'Wrong! Finally, what is her favorite thing to do?"

'Um...swim?"

"Close, but no. The final score is 3/5! Next up, Conway will be answering the questions."

Conway had an evil, stalkerish glint in his eye.

"Favorite color? Pink, but also black. She can't decide."

"Correct. What are her parents' names."

"She only has a mom and her name is Johanna."

"Correct. Where is she from?"

"Easy. Twinleaf town."

"Correct. Favorite food?'

"She claims that it's nutrition bars, but she really likes to stuff her face with icecream when no one's around."

"Correct. What is her favorite thing to do?"

"Besides styling her hair, she loves to enter contests and secretly writes poetry."

"Correct! Five out of five!"

Dawn shivered as Conway sat down next to her.

"How do you know all that stuff about me?"

"Research. By the way, I liked your latest poem. 'Stalker' I believe it was titled.

"Alright. Now it's Ash turn! What is her favorite color?"

"Red!"

"Correct. How about her parents' names?"

"Caroline and Norman Maple."

"Where is she from?"

"Petalburg."

"Favorite food?"

"Food would be ramen. Candy is Pocky."

"Correct. Lastly, her favorite thing to do?"

"Crossdress."

"That's a bit odd, but correct! Conway and Ash are tied for points. Team Misty and Tracey are eliminated. The deciding factor will be how well the girls know the guys."

"Dawn. What's his favorite color?"

"Um...Green?"

"Wrong."

"Yup. I like red, blood red."

"Next, what are his parents' names?"

"How should I know?"

"There names are Connie and Steven," answered Conway.

"Ok. Where is he from?"

"A dark cave where no one should enter?"

"That's wrong, but I'd rather let YOU guess where I live."

"What's his favorite food?"

"Sub?"

"Wrong. I feel in touch with you, so I eat icecream as well."

"Finally, what's his favorite thing to do?"

"Stalk me?!"

"Correct! That's one point for Dawn and Conway. It all comes down to May..."

May took a deep breath and nodded at Drew, signalling that she was ready.

"Favorite color?"

"Blue. He's always wearing it."

"Correct. Parents' names?"

"He doesn't know his dad, but his mom is Delia."

"Correct. Where is Ash from?"

"Pallet town."

"Favorite food?'

"Every food known to man."

"Correct. Finally, what's his favorite thing to do?"

"Be an awesome boyfriends and always do fun things with me"

"Correct! Ash and May win with a perfect score!"

The crowd cheered loudly. May grabbed Ash's shirt collar, pulling him forward and into a kiss.

"Good things always happen when I crossdress," giglled May.

"I'll say," said Ash, smiling.

And that was how it ends. They lived together for the rest of their lives and May crossdressed until she was 25. Ash always thought that crossdressing was their good luck charm. The End.


End file.
